[Conformationally restricted pethidine analogs. 5. Synthesis and pharmacologic testing of cis-B-10b-acyl-1,2,3,4,4a,5,6,10b- octahydrobenzo(f)isoquinolines]. / Pethidin-Analoga mit eingeschränkter Konformationsbeweglichkeit. 5. Mitteilung: Synthese und pharmacokologische Prüfung von cis-B-10b-Acyl-1,2,3,4,4a,5,6,10b-octahydrobenzo[f]ischinolinen.

Cyanophenylcyclobuten (1a) gave the corresponding cis-B-configurated 10b-acyloctahydrobenzo[f] isoquinolines 3a-f by Grignard reaction. Cis-B-3b was demethylated to yield the secondary base 3g, which in turn was realkylated to the homologous allyl- and isopentenyl derivatives 3h and 3i. In the writing test the desoxyketobemidon analogon cis-B-3b exhibits a remarkable activity, whereas 3a, c-e are somewhat weaker and 3h and 3i are inactive.